4-Amino-5-(4-methyl-benzyl)-2,4-dihydro-[1,2,4]triazol-3-one | 147440-64-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-Amino-5-(4-methyl-benzyl)-2,4-dihydro-[1,2,4]triazol-3-one
• 英文别名: 4-amino-3-[(4-methylphenyl)methyl]-1H-1,2,4-triazol-5-one
• CAS: 147440-64-0
• 化学式: C₁₀H₁₂N₄O
• 分子量: 204.231
• InChiKey: AVBVEORJUQWPQF-UHFFFAOYSA-N

物化性质

• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.18
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  76.7
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-Amino-5-(4-methyl-benzyl)-2,4-dihydro-[1,2,4]triazol-3-one 在 溶剂黄146 作用下， 反应 2.0h， 生成 4-({[1-acetyl-3-(4-methylbenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-4-yl]imino}methyl)phenyl 4-nitrobenzoate
  参考文献：
  名称：

  Synthesis and Antioxidant and Antibacterial Activities of Novel 4-({[3-Alkyl(aryl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-4-yl]imino}­methyl)phenyl 4-Nitrobenzoate Derivatives

  摘要：

  DOI：

  10.1134/s1070428022120132
• 作为产物：
  描述：

  在 一水合肼 作用下， 以 水 为溶剂， 反应 0.05h， 生成 4-Amino-5-(4-methyl-benzyl)-2,4-dihydro-[1,2,4]triazol-3-one
  参考文献：
  名称：

  微波和常规方法合成含有靛红作为潜在抗菌剂和抗真菌剂的新型三唑化合物

  摘要：

  微波辐射已被用于加速靛红 (1a) 和 5-硝基靛红 (1b) 转化为它们的希夫碱 3-[5'-芳基(烷基)-2',4'-二氢-1',2', 4'-triazol-3'-on-4'-yl]iminoisatin (3a–g) 和 3-[5'-aryl(烷基)-2',4'-dihydro-1',2',4'- triazol-3'-on-4'-yl]imino-5-nitroisatin (4a–g) 分别。反应采用微波诱导技术，与传统加热相比，大大缩短了反应时间，提高了产率。新合成的碱基对所测试的标准细菌和真菌生物显示出中等的抗菌活性

  DOI：

  10.3184/174751911x13043524455143

文献信息

• Synthesis and in vitro antioxidant and antimicrobial activities of novel 3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones, and their N-acetyl, N-Mannich base derivatives
  作者：Sevda Manap

  DOI：10.1007/s13738-021-02386-7

  日期：2022.4

  The reactions of 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (1) with 3-methoxy-4-(2-furylcarbonyloxy)-benzaldehyde (2) formed 3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones (3). Moreover, their five N-acetyl derivatives were synthesized. Besides, 1-(morpholine-4-yl-methyl)-3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones (5)/1-(4-methylpiperazin-1-yl-methyl)-3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones (6)/1-(piperidine-4-carboxyamide-1-yl-methyl)-3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones (7)/N,N′-bis-3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylideneamino]-4,5-dihydro-1H-1,2,4-triazol-5-on-1-yl-methyl}-piperazines (8) were obtained by Mannich reaction between compounds 3 and morpholine/N-methylpiperazine/piperidine-4-carboxyamide/piperazine in the presence of formaldehyde. The newly obtained thirty-four compounds were characterized from IR, 1H NMR, 13C NMR, and MS spectral data. Also, these compounds were evaluated for their in vitro antioxidant activity. Furthermore, in vitro antibacterial activity of the compounds was screened against six bacteria.

  3- 烷基（芳基）-4-氨基-4,5-二氢-1H-1,2,4-三唑-5-酮 (1) 与 3-甲氧基-4-（2-呋喃甲酰氧基）-苯甲醛 (2) 反应生成了 3-烷基（芳基）-4-[3-甲氧基-4-（2-呋喃甲酰氧基）-亚苄基氨基]-4,5-二氢-1H-1,2,4-三唑-5-酮 (3)。此外，还合成了它们的五个 N-乙酰基衍生物。此外，还合成了 1-(吗啉-4-基-甲基)-3-烷基(芳基)-4-[3-甲氧基-4-(2-呋喃甲酰氧基)-亚苄基氨基]-4,5-二氢-1H-1,2,4-三唑-5-酮 (5)/1-(4- 甲基哌嗪-1-基-甲基)-3-烷基(芳基)-4-[3-甲氧基-4-(2-呋喃甲酰氧基)-亚苄基氨基]-4,5-二氢-1H-1,2,4-三唑-5-酮 (6)、5-dihydro-1H-1,2,4-triazol-5-ones (7)/N,N′-bis-3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylideneamino]-4,5-dihydro-1H-1,2,化合物 3 与吗啉/N-甲基哌嗪/哌啶-4-羧酰胺/哌嗪在甲醛存在下发生曼尼希反应，得到了 4,5-二氢-1H-1,2,4-三唑-5-on-1-基-甲基}-哌嗪（8）。根据红外光谱、1H NMR、13C NMR 和 MS 光谱数据对新得到的 34 种化合物进行了表征。此外，还对这些化合物的体外抗氧化活性进行了评估。此外，还筛选了这些化合物对六种细菌的体外抗菌活性。
• Synthesis, design, and assessment of novel morpholine-derived Mannich bases as multifunctional agents for the potential enzyme inhibitory properties including docking study
  作者：Songül Boy、Fikret Türkan、Murat Beytur、Abdülmelik Aras、Onur Akyıldırım、Halide Sedef Karaman、Haydar Yüksek

  DOI：10.1016/j.bioorg.2020.104524

  日期：2021.2

  The synthesized Schiff Bases were reacted with formaldehyde and secondary amine such as 2,6-dimethylmorpholine to afford N-Mannich bases through the Mannich reaction. 3-Substitued-4-(4-hydroxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones (4) were treated with 2,6-dimethylmorpholine in the presence of formaldehyde to synthesize eight new 1-(2,6-dimethylmorpholino-4-yl-methyl)-3-substitued-4-

  合成的席夫碱与甲醛和仲胺如2,6-二甲基吗啉反应，通过曼尼希反应得到N-曼尼希碱。3-取代的-4-（4- hydroxybenzylidenamino）-4,5-二氢-1- ħ -1,2,4-三唑-5-酮（4）在甲醛存在下，以合成用2,6-二甲基吗啉处理八种新的 1-(2,6-dimethylmorpholino-4-yl-methyl)-3-subSTitued-4-(4-hydroxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones ( 4a-h)。合成的8个新化合物的结构使用IR、1 H NMR、13C NMR和HR-MS光谱方法。合成化合物对乙酰胆碱酯酶 (AChE)、丁酰胆碱酯酶 (BChE) 和谷胱甘肽 S-转移酶 (GST) 的抑制活性测定，AChE 的 Ki 值范围为 25.23-42.19 µM，BChE.8 的 Ki
• Synthesis, Spectroscopic Analysis, and <i>in Vitro/in Silico</i> Biological Studies of Novel Piperidine Derivatives Heterocyclic Schiff‐Mannich Base Compounds
  作者：Songül Boy、Abdülmelik Aras、Fikret Türkan、Onur Akyıldırım、Murat Beytur、Halide Sedef Karaman、Sevda Manap、Haydar Yüksek

  DOI：10.1002/cbdv.202100433

  日期：2021.12

  to afford novel heterocyclic bases. 3-Substitued-4-(4-hydroxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones (T) were treated with 4-piperidinecarboxyamide in the presence of formaldehyde to synthesize eight new 1-(4-piperidinecarboxyamide-1-yl-methyl)-3-substitued-4-(4-hydroxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones (M1-8). The structure characterization of compounds was carried out

  在本研究中，通过处理 4-羟基苯甲醛（B )在乙酸介质中分别使用八种不同的 3-取代-4-氨基-4,5-二氢-1 H -1,2,4-三唑-5-酮 ( T1-8 )。合成的席夫碱( S )与甲醛和仲胺如4-哌啶甲酰胺反应得到新型杂环碱。3-取代-4-(4-羟基苄基氨基)-4,5-dihydro-1 H -1,2,4-triazol-5-ones ( T)在甲醛存在下用4-哌啶甲酰胺处理合成8个新的1-(4-哌啶甲酰胺-1-基-甲基)-3-取代-4-(4-羟基苄基氨基)-4,5-二氢-1H -1,2,4-triazol -5-ones ( M1-8 )。化合物的结构表征使用1 H-NMR、IR、HR-MS 和13 C-NMR 光谱方法进行。计算了新合成的化合物对乙酰胆碱酯酶 (AChE)、丁酰胆碱酯酶 (BChE) 和谷胱甘肽 S-转移酶 (GST) 酶的抑制特性。Ki 值的计算范围为 GST
• Synthesis,<i>In Vitro</i>Antimicrobial and Antioxidant Activities of Some New 4,5-Dihydro-1<i>H</i>-1,2,4-triazol-5-one Derivatives
  作者：Haydar Yüksek、Onur Akyıldırım、Mehmet L. Yola、Özlem Gürsoy-Kol、Mustafa Çelebier、Didem Kart

  DOI：10.1002/ardp.201300048

  日期：2013.6

  series of compounds derived from 4,5‐dihydro‐1H‐1,2,4‐triazol‐5‐one were synthesized and characterized by spectral data. The 12 new compounds were analyzed for their potential in vitro antioxidant activities by three different methods. Compound 4f showed the best activity for the iron binding. In addition, the compounds 4 were titrated potentiometrically with tetrabutylammonium hydroxide in non‐aqueous

  合成了一系列衍生自 4,5-dihydro-1H-1,2,4-triazol-5-one 的化合物，并通过光谱数据表征。通过三种不同的方法分析了 12 种新化合物的潜在体外抗氧化活性。化合物4f显示出最佳的铁结合活性。此外，化合物 4 在非水溶剂中用四丁基氢氧化铵进行电位滴定。该系列的 RP-HPLC 容量因子 (k') 也在 C18 柱上测定，甲醇/水作为流动相。log k' 与流动相中甲醇百分比之间的相关性用于确定这些化合物的 log kw 值。还筛选了这些化合物对细菌和酵母菌的抗微生物活性。
• Synthesis, Acidity and Antioxidant Properties of Some Novel 3,4-disubstituted-4,5-dihydro-1H-1,2,4-triazol-5-one Derivatives
  作者：Muzaffer Alkan、Haydar Yüksek、Özlem Gürsoy-Kol、Mustafa Calapoğlu

  DOI：10.3390/molecules13010107

  日期：——

  3-Alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones 2a-g reacted with4-diethylaminobenzaldehyde to afford the corresponding 3-alkyl(aryl)-4-(4-diethylaminobenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones 3a-g. The acetylationreactions of compounds 3a-e were investigated and compounds 4a-e were thus obtained.The new compounds were characterized using IR, 1H-NMR, 13C-NMR, UV and MSspectral data. In addition, the newly synthesized compounds 3a-g were titratedpotentiometrically with tetrabutylammonium hydroxide in four non-aqueous solvents suchas isopropyl alcohol, tert-butyl alcohol, acetone and N,N-dimethylformamide (DMF), andthe half-neutralization potential values and the corresponding pKa values were determinedfor all cases. Moreover, 3 and 4 type compounds were also screened for their antioxidantactivities.

  3-烷基(芳基)-4-氨基-4,5-二氢-1H-1,2,4-三唑-5-酮2a-g与4-二乙氨基苯甲醛反应得到相应的3-烷基(芳基)-4- (4-二乙氨基亚苄基氨基)-4,5-二氢-1H-1,2,4-三唑-5-酮3a-g。研究了化合物3a-e的乙酰化反应，得到了化合物4a-e。利用IR、1H-NMR、13C-NMR、UV和MS光谱数据对新化合物进行了表征。此外，在异丙醇、叔丁醇、丙酮和N,N-二甲基甲酰胺(DMF)四种非水溶剂中，用四丁基氢氧化铵对新合成的化合物3a-g进行电位滴定，得到半中和电位值和相应的半中和电位值。确定所有情况的 pKa 值。此外，还筛选了3型和4型化合物的抗氧化活性。